CA2423357C - Fused heterocyclic derivatives as phosphodiesterase inhibitors - Google Patents
Fused heterocyclic derivatives as phosphodiesterase inhibitors Download PDFInfo
- Publication number
- CA2423357C CA2423357C CA002423357A CA2423357A CA2423357C CA 2423357 C CA2423357 C CA 2423357C CA 002423357 A CA002423357 A CA 002423357A CA 2423357 A CA2423357 A CA 2423357A CA 2423357 C CA2423357 C CA 2423357C
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- CA
- Canada
- Prior art keywords
- group
- compound
- pyrido
- benzo
- dioxol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000623 heterocyclic group Chemical group 0.000 title description 3
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 title description 2
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- 150000003839 salts Chemical class 0.000 claims abstract description 27
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- -1 haloC1-6-alkyl Chemical group 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 230000002829 reductive effect Effects 0.000 claims description 20
- 229910052757 nitrogen Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
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- XMDPDVFDENOQLG-CSODHUTKSA-N (3s,6r,12ar)-3-(2-aminoethyl)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@@H]3C(=O)N[C@H](C(N32)=O)CCN)=C1 XMDPDVFDENOQLG-CSODHUTKSA-N 0.000 claims 1
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- ZDSNTZVDVXETRU-DLCOBIQGSA-N (6r,12ar)-6-(1,3-benzodioxol-5-yl)-3-(pyrazol-1-ylmethyl)-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound O=C([C@@H]1N([C@@H](C2=C(C3=CC=CC=C3N2)C1)C=1C=C2OCOC2=CC=1)C1=O)NC1CN1C=CC=N1 ZDSNTZVDVXETRU-DLCOBIQGSA-N 0.000 claims 1
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Otolaryngology (AREA)
- Gynecology & Obstetrics (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22245100P | 2000-08-02 | 2000-08-02 | |
| US60/222,451 | 2000-08-02 | ||
| PCT/US2001/021678 WO2002010166A1 (en) | 2000-08-02 | 2001-07-09 | Fused heterocyclic derivatives as phosphodiesterase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2423357A1 CA2423357A1 (en) | 2002-02-07 |
| CA2423357C true CA2423357C (en) | 2008-05-27 |
Family
ID=22832258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002423357A Expired - Fee Related CA2423357C (en) | 2000-08-02 | 2001-07-09 | Fused heterocyclic derivatives as phosphodiesterase inhibitors |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7034027B2 (https=) |
| EP (1) | EP1305313A1 (https=) |
| JP (1) | JP4220775B2 (https=) |
| AU (1) | AU2001271948A1 (https=) |
| CA (1) | CA2423357C (https=) |
| MX (1) | MXPA03000887A (https=) |
| WO (1) | WO2002010166A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004054560A1 (en) | 2002-12-13 | 2004-07-01 | Warner-Lambert Company Llc | Alpha-2-delta ligand to treat lower urinary tract symptoms |
| BRPI0506994A (pt) | 2004-01-22 | 2007-07-03 | Pfizer | derivados de triazol que inibem a atividade antagonista da vasopressina |
| WO2007100387A2 (en) * | 2005-11-03 | 2007-09-07 | Dr. Reddy's Laboratories Ltd. | Process for preparing tadalafil |
| WO2010015585A1 (en) * | 2008-08-05 | 2010-02-11 | Nycomed Gmbh | 6-benzyl-2,3,4,7-tetrahydro-indolo[2,3-c]quinoline compounds |
| US20160317542A1 (en) | 2013-12-09 | 2016-11-03 | Respira Therapeutics, Inc. | Pde5 inhibitor powder formulations and methods relating thereto |
| ES2774048T3 (es) * | 2015-06-26 | 2020-07-16 | Chongqing Dikang Erle Pharma Co Ltd | Nuevo inhibidor de la fosfodiesterasa de tipo 5 y su aplicación |
| US11505531B2 (en) * | 2018-08-07 | 2022-11-22 | Uab Research Foundation | Piperazine-2,5-diones as TGF-beta inhibitors |
| CN113999228B (zh) * | 2021-11-08 | 2022-11-04 | 南京卓康医药科技有限公司 | 一种他达拉非的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9401090D0 (en) * | 1994-01-21 | 1994-03-16 | Glaxo Lab Sa | Chemical compounds |
| GB9514465D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
| GB9514464D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Medicaments |
| US6046199A (en) | 1998-01-14 | 2000-04-04 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B]indole derivatives |
| US6225315B1 (en) * | 1998-11-30 | 2001-05-01 | Pfizer Inc | Method of treating nitrate-induced tolerance |
| ES2187234A1 (es) * | 1999-04-30 | 2003-05-16 | Lilly Icos Llc | Forma de dosificacion oral para tratar la disfuncion sexual. |
| CA2365782A1 (en) * | 1999-04-30 | 2000-11-09 | William E. Pullman | Treatment of female arousal disorder |
-
2001
- 2001-07-09 EP EP01951008A patent/EP1305313A1/en not_active Withdrawn
- 2001-07-09 CA CA002423357A patent/CA2423357C/en not_active Expired - Fee Related
- 2001-07-09 MX MXPA03000887A patent/MXPA03000887A/es active IP Right Grant
- 2001-07-09 WO PCT/US2001/021678 patent/WO2002010166A1/en not_active Ceased
- 2001-07-09 US US10/333,146 patent/US7034027B2/en not_active Expired - Fee Related
- 2001-07-09 JP JP2002515895A patent/JP4220775B2/ja not_active Expired - Fee Related
- 2001-07-09 AU AU2001271948A patent/AU2001271948A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP4220775B2 (ja) | 2009-02-04 |
| US7034027B2 (en) | 2006-04-25 |
| AU2001271948A1 (en) | 2002-02-13 |
| EP1305313A1 (en) | 2003-05-02 |
| US20030207867A1 (en) | 2003-11-06 |
| JP2004505083A (ja) | 2004-02-19 |
| MXPA03000887A (es) | 2004-04-05 |
| WO2002010166A1 (en) | 2002-02-07 |
| CA2423357A1 (en) | 2002-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |